


Double Trouble

by TobytheWise



Series: Tobys ABO Bingo [1]
Category: Supernatural
Genre: Alpha Castiel (Supernatural), Alpha Jimmy Novak, Bottom Castiel, Bottom Dean, Bottom Jimmy Novak, Cock Cages, Dildos, Dom Dean Winchester, Handcuffs, M/M, Mpreg, Multi, Omega Dean, Punishment, Restraints, Strap-Ons, Stripper Castiel, Vibrators, stripper jimmy
Language: English
Status: Completed
Published: 2018-07-19
Updated: 2018-07-19
Packaged: 2019-06-13 00:54:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,722
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/15352623
Author URL: https://archiveofourown.org/users/TobytheWise/pseuds/TobytheWise
Summary: Dean whimpers when both alphas lift themselves from his lap. They smile so innocently at him from beneath their eyelashes.“Thank you, Sir,” Jimmy says.“Have a good night. I hope you enjoyed your dance,” Cas says with a grin before they both walk out the door leaving Dean painfully hard and embarrassingly wet. Oh, they are gonna regret this….ORthe one where Dean visits his favorite strippers. They tease him mercilessly until he's left hard, wet, and needy. Good thing when the twins get home, Dean will be able to enjoy every second of punishing them.





	Double Trouble

**Author's Note:**

  * For [ladyofthursday](https://archiveofourown.org/users/ladyofthursday/gifts).



> This is a birthday gift to my favorite person, LadyofThursday! I love you and I hope you love this yumminess!
> 
> Written for SPNABOBingo  
> Square filled: Toys

Dean is going to have a heart palpitation and die. His heart is going to literally beat right out of his chest and they will have to make up a dumbass story about the dumbass guy who died at the strip club from heart failure. And yet, here Dean is, sitting in the front row. 

Dean’s pants are so tight in the front they’re starting to hurt and his hole clenches, begging to be filled. His chest feels tight and he knows he’s starting to sweat. He doesn’t care. Right now, the most gorgeous alpha he’s ever laid eyes on is dancing and he can’t pull his eyes away. 

The way the man’s hips move, the way his hair is a completely beautiful brunette mess, the way his eyes almost seem to light up with an unworldly blue. Everything about this man is mesmerizing. 

Dean wishes he could pull his thickened cock out and rub one out while watching those thick runner thighs move in front of his face. 

Tall, dark, and handsome is currently doing a spinning move on the pole and Dean knows his mouth is open like an idiot but he can’t seem to make his brain work at the moment. He feels like he’s under a spell and the only thing getting him out is seeing this man up close and personal.

As soon as the man is done with his routine and gone behind the curtain, Dean is moving back to the closed off area, the part of the club that allows personal dances. Dean would willingly spend every penny in his savings account to spend time with that brown haired beauty that just performed.

Once Dean’s paid the bouncer, he looks around the private room. It’s nothing special. He sits down on the red couch that’s in the middle of the room and waits for the embodiment of his every wet dreams to come in.

As he’s stretching his arms across the back of the couch, the door opens and the blue eyed angel of Dean’s dreams walks in. He’s dressed in white short shorts and a beautiful pair of white wings strapped to his back. He’s gorgeous. 

“Fuck,” Dean whispers to himself as the man smirks at him. Then he turns and cracks the door open. That’s when Dean’s pretty sure this is a hallucination or dream or he’s already died and gone to heaven because in walks another blue eyed angel. Twins. This one has a similar outfit on but in black. The twins look at each other, having a silent conversation before turning their matching, predatory eyes towards Dean. He’s so screwed. 

“Hello, Handsome,” the alpha wearing the black purrs at him. 

“Hi,” Dean barely manages to get out. His mouth is dry and his tongue feels two sizes too big. These two are going to be the death of him, which is fitting as they’re clearly angels of death!

The angel in white clicks on the stereo causing low, pulsing beats to fill the room. Dean barely even registers the music because the angels are staring at each other with heat in their eyes. The musky smell of alpha arousal begins to permeate the room, Dean takes it in greedily and lets it overtake his other senses. He lets out a low groan as his cock twitches in his jeans. 

“Hmm, I think our omega likes what he sees,” the angel in black murmurs. “What do you think Jimmy? Should we put on a special show for him?”

The angel in white, Jimmy, grins over at Dean before looking back at the angel in black. “I think he would love that, Cas.” Jimmy turns his back to Cas and begins to grind his ass against Cas’ front. It’s so fucking hot to see two alphas like this. 

“Oh, shit,” Dean whispers Cas begins to kiss the back of Jimmy’s neck. Jimmy lets out the most breathtaking whimper it makes Dean’s hole begin to slick up. He’s thankfully wearing his ‘omega panties’ that will absorb his slick and the room hopefully won’t fill with the scent of his slick. He squirms in his seat, watching as the alphas begin to dance seductively with each other. Their hands are caressing and touching the other in the most intimate way. They’re beautiful.

“Jimmy, why don’t you go give our omega a proper lap dance?”

Jimmy smiles before sensually stalking his way over to where Dean is sitting. He spreads his legs, making room for the alpha to dance. And dance he does. Dean watches, mesmerized by the smooth rhythm of Jimmy’s hips. Jimmy turns, ever so slowly, until his perfect, perky ass is shaking right in front of Dean’s face and the omega’s mouth waters, thinking of all the dirty things he’d love to do with that ass. 

Cas wanders over to his brother, running his hands down Jimmy’s back and grabbing two handfuls of his ass. Dean groans, eyes glued to where Cas’ hands massage his twin’s cheeks. Grinding against each other, the blue eyed angels begin to make little moans and Dean feels like his cock is ready to explode at any moment. 

Jimmy pulls Cas into a heated kiss as they continue to sway against each other. They turn, giving Dean the perfect view of their bodies and their intertwining tongues. “So fucking sexy,” he murmurs. He can see both of their hard cocks through their little shorts, his ass clenches just imagining them inside him.

Dean moves his hand to touch his cock through his jean but a hand quickly grabs his wrist. “I’m sorry sir, but we don’t allow our customers to get ‘handsy’,” Cas says with a wicked smile. Dean glares daggers at the alpha which only results in both twins to chuckle at him. 

He’s about to say something about the customer always being right but no words come out when he’s got a lapful of angel twins. Jimmy is straddling one of his legs facing him. His other leg is straddled by Cas who’s facing away, giving Dean the perfect view of his gorgeous ass. 

The twins dance and it’s nothing Dean’s ever experienced before. Their musky, arousal amplifying Dean’s lust higher and higher. Dean’s not sure he can take much more of this when the twins turn and begin to kiss each other right in front of Dean’s face. Jimmy grinds his hard cock down against Dean’s thigh and tenses. Seconds later, Dean can smell the heady scent of alpha cum in the air. Cas grinds his ass down hard against Dean’s thigh at the same time. Filling his short shorts with cum just as Jimmy leans over and bites down on his neck. 

Dean whimpers when both alphas lift themselves from his lap. They smile so innocently at him from beneath their eyelashes. 

“Thank you, Sir,” Jimmy says.

“Have a good night. I hope you enjoyed your dance,” Cas says with a grin before they both walk out the door leaving Dean painfully hard and embarrassingly wet. Oh, they are gonna regret this….

###

The twins are laughing about something as they walk through the front door.  _ They won’t be laughing for long,  _ Dean thinks to himself. They don’t even seem to notice that he’s up and waiting for them until they walk in the bedroom. 

“Hello, my alphas,” he says as they finally notice him sitting in the armchair in their room. 

Castiel and Jimmy stop in their tracks, eyes roaming around the room, taking in the various toys Dean’s laid out for them. Dean doesn’t even try to stop the smirk from spreading across his face. This is going to be fun.

“Strip,” Dean demands as he gets up from his chair. Both alphas quickly strip until they’re bare. Their heads are down respectfully. “You both decided it would be a good idea to tease your omega tonight. I came to see my favorite angels perform. I wanted to spend some time with you both and admire just how fucking beautiful you are.” Dean walks around them, occasionally running his hand along some part of their skin. “And how do you repay me for that kindness? By teasing your thoughtful mate? Leaving him hard and needy and wet?” Dean pulls his hand back, first slapping Cas’ ass and then Jimmy’s, loving the sharp double intake of breathes and the bright red handmark he’s left behind. “And to think, I had a lovely surprise for you both. A big secret to reveal that would have made tonight so fucking special.” He spanks them again, leaving matching prints on their other cheeks. “But now I’m gonna enjoy myself while punishing the hell out of you,” he finishes with a giant smile.

Dean inhaled sharply, taking in the scent of aroused alpha. “You both wanted to be punished today, didn’t you?” he accuses. Jimmy twitches but neither say anything. “Speak, now!”

“Yes, Sir,” Jimmy whispers. “We were both horny and knew that teasing you like that would lead to some sort of punishment. We were both hoping you’d give us a spanking or something.”

“Cas?”

“It’s true, Sir. We haven’t played in awhile and we were hoping teasing you would lead to playing.”

Finally Dean smells something other than the musky scent of arousal, embarrassment and guilt. 

Dean runs his fingers through his hair in frustration. “If you wanted to play you  _ talk _ to me! You don’t force my hand like this!” He walks until he’s in front of his alphas. He tilts their heads up so he can look into their eyes. “Next time, I expect a conversation. Not this bullshit you pulled today. And there’s a reason we haven’t been playing lately,” he murmurs, more to himself. 

“I’m sorry, Sir,” Jimmy whispers and Dean smells the remorse, he really is sorry. Good.

“Me too, Dean. I’m sorry.”

Dean takes a deep breath, steadying himself. “Jimmy, lay down on your back.” Jimmy complies immediately as Cas continues to stand at the end of the bed, watching with wide eyes as Dean grabs one of the small boxes on the bed. 

Dean smiles as he grabs an ice cube from the cup on the nightstand. He cups it in his hand as he holds Jimmy dick. The alpha hisses but his cock goes flaccid, just like Dean knew it would. Then he slides the metal ring to the base of Jimmy’s cock before placing the second part of the cage in place. Finally, he snaps the lock shut. “Your cock looks so pretty all soft for me, Jimmy.”

The alpha whimpers at Dean’s words and Dean grins. He taps Jimmy’s hip in mock sympathy. 

“Switch, boys,” he says, watching as Jimmy’s soft cock rests perfectly against his big alpha balls as he moves to stand at the end of the bed. Castiel lays down, eyes squeezed shut tight. Dean makes quick work of locking Cas’ cock up in its new cage. “There we go. All pretty for me. Go stand by your brother.”

Dean grabs the next thing off the bed. He walks in front of Jimmy. When he kneels down at his feet, Jimmy moans but Dean just rolls his eyes because that’s NOT why Dean is down here! Dean takes the harness he bought, making Jimmy step into it and sliding it up Jimmy’s legs and thighs until it’s snugly in place. He slides over and does the same for Cas. When he stands Dean can smell their confusion and it makes him smile. 

“Cas, up on the bed, on your back, head up by the headboard. Jimmy, up on the bed, on your back, head by the baseboard.”

The alphas hurry to get into position. Their bed is just the right size for what Dean has planned. He can feel his hole begin to slick as his excitement rises. He’s been horny for so long and he’s so excited to feel relief, finally. 

Dean takes the handcuffs he has on the bed, snapping them in place around Castiel’s wrists and through the headboard, keeping the alpha in place. He does the same for Jimmy at the baseboard. Their legs overlap and touch, their asses just barely not touching. Perfect. 

“Because I am a kind and gracious omega, I’ve decided to allow you some pleasure,” Dean says as he holds up a small, double ended dildo. “Color?”

“Green, Sir,” comes the unison answer. 

Dean slicks his fingers up, working the alphas open quickly before sliding the dildo into Castiel’s ass first. Then maneuvering it so he can insert the other end into Jimmy. Both alphas groan, enjoying their holes played with. Dean chuckles as he smells their arousal intermingled with frustration, knowing their cocks won’t get hard and their knots won’t be able to pop. 

“Just because you both can’t get hard doesn’t mean  _ I _ should be punished,” Dean says as he takes out two of their smaller dildos. He puts them into his alphas’ harnesses. Their asses are close enough that the dildo line up next to each other and Dean knows he’ll be able to take both of them. 

Dean knows all of Jimmy and Castiel’s preferences and chooses to do the opposite. He faces Castiel since Cas loves to see the sight of his cock going into Dean’s ass. His ass towards Jimmy since he usually loves to watch all of Dean’s reactions. 

“Mmm,” Dean hums as he slowly backs his ass up against the head of the dildos. He gently slides down, reveling in the feel of finally being filled. His slick drips down, coating the dildos and sliding down onto his mates’ hips. 

The alphas moan, watching Dean ride their silicon cocks. The smell of frustration slowly growing stronger and Dean absolutely loves it. 

“Please,” he hears Jimmy whimper. Dean grabs the remote next to Castiel’s head and hits the on button. Both alphas jerk hard against their restraints, squirming as much as they can as the dildo inside their ass begins to vibrate. The scent of arousal begins to overtake the smell of frustration causing Dean to ride the dildos even harder. 

“Oh fuck,” Dean moans, throwing his head back in pleasure. “You guys can come at anytime if you can. Don’t hold back.” Cas’ body tenses but Dean doesn’t smell any cum. 

“I can’t,” Jimmy whimpers. “Dean, please!”

Dean turns the vibrations up another notch and thoroughly enjoys the alphas’ broken moans and delicious scent. 

“I’m gonna come and then I’m turning the vibrations off,” Dean states breathlessly. He continues riding the dildo hard, striping his cock. He tilts his hips perfectly so the dildos rub his prostate just right. “Oh shit. Yes,” Dean grits through his teeth as he comes, dirtying Cas’ belly with his cum. 

Once he’s done, Dean slumps down. He turns the vibrator off before pulling up and allowing the dildos to slide from his ass. He knows he smells of happy, sated, omega and he hopes that will calm his alphas down but he’s surprised when he looks at them and finds them both relaxed with their eyes closed, almost like they’re enjoying the post orgasmic glow without the scent of alpha cum.

Dean takes his time removing the restraints, the dildo, the harness, everything but the cages. Those are going to stay for a few days, Dean thinks. He wipes them down before snuggling down between them. They both wrap their arms around Dean, scenting him and kissing the mating bites on his neck. 

“We’re sorry, baby,” Cas murmurs against the back of his neck. “We didn’t mean to be such brats. We thought it would be fun but we went too far.”

“Yeah,” Jimmy adds. “Next time we’ll just talk to you.”

“Thank you,” Dean whispers, suddenly overcome with emotions. “I love you both so fucking much.”

The arms around him tighten. “We love you too, Dean,” Jimmy says, adding a kiss to Dean’s forehead. 

“What was the good news you wanted to tell us?” Castiel asks. 

Dean lets out a watery chuckle. “The reason I haven’t wanted to play lately is because I’ve been feeling so fucking sick and so tired. Turns out there’s a reason for that,” Dean pauses so he can sit up and look at both of his mates, smiling so big his cheeks hurt. “I’m pregnant!”


End file.
